Stranger
by Sadleah
Summary: Pre-slash What happens when you combine a bust of a date and an international Portkey.
1. Chapter 1

Harry let out a strong sigh, he shouldn't have trusted Hermione to set him up on a blind date, he hasn't dated since the war and if he was honest he couldn't find a fault in that. Everyone was so sure Harry was lonely and needed someone to settle down, and have kids with. It was like they wanted him to completely forget the war! Sure he was happy for Ron and Hermione and he loved Victorie but that did not mean he wanted his own lot of Potters, running around. Teddy was enough, thank you very much.

He wasn't even completely straight, but merlin forbid Hermione even try to set him up with someone of his own gender. Thank you muggle upbringing for rearing your ugly head at all the worst moments. Perhaps he'd be content if Hermione had set him up with a muggle, but no, a muggle would not be permanent so my options are quite limited. Harry was fed up with waiting for a date who wasn't showing, not that he blamed them, every date he'd ever been on seems to find its way onto the pages of _Witches Weekly_ , and everyone knows his sordid love affairs. With that he took off, the Portkey wouldn't leave for another few hours, and really Hermione, high hopes much, meaning he was stuck in who knows where New York. Honestly, what a joke, an international portkey for a date, stupid kingsley and his weak will.

He walked around for some time before spotting a place that looked promising enough _The Empire Hotel_ , Hotels have bars right? He shrugged, walking in finding the bar rather quickly. He seated himself and looked around, glad Hermione insisted she dress him as he fit right in decked out in Alexander McQueen. He ordered a glass of whisky, paying with his Gringotts Unlimited card.

He was staring into his glass of amber, taking an occasional sip, counting down the minutes until the portkey would activate. A smooth baritone interrupted his inner turmoil, sliding into the open seat to his left "Ah, a man after my own heart." When Harry looked up, he admitted to himself that the man was good looking, but he had a look of condescending snobbery only gained from being raised with an exponential wealth, the likes of which he'd only ever seen on pre-war malfoy. Harry raised an eyebrow at the man "Yes well it's a bit weak for my taste, but I grew up drinking local, much stronger than anything you could get here."

The man chuckled, extending his hand, claiming almost expectantly "I'm Chuck Bass". Harry rolled his eyes at the ego on the man, honestly. He contemplated ignoring the man, but some part of him was enjoying this, whatever the hell this was. He grabbed the others hand, not expecting for the guy to kiss it. He quickly pulled back his hand, glaring at the man's audacity. "Harry Potter" he replied, not enjoying the amused glint in the others eyes.

"So why are you in town Harry?" Chuck asked, continuing before Harry had the chance to retort "It's just you don't recognize me and not many people can say that, not in these parts of town at least." Harry just scoffed "You're rather presumptuous, I could very well live here for all you know." If anything that comment seemed to amuse him further "not likely" chuck replied in an infuriating tone. "And why not?" Harry challenged regretting it the moment a predatory smirk graced the others lips "I'm Chuck Bass, I own this place." Damn it. He really needed to do more research on a place before gallivanting off into the night. Harry released a small huff, a light blush coating his cheeks "My point remains." Chuck flashed him an amused look "As does my question, business or pleasure Mr. Potter?"

"Neither." Harry replied forcefully. Chuck turned to him a single eyebrow raised, "Oh?" a clear invitation to continue. What the hell? Harry figured he'd never see this man again. Famous last words.

Three hours and 5 glasses later, his Portkey was set to take off in 5 minutes. In a truly cinderella fashion harry scribbled his name and phone number across a cocktail napkin and shoved it into Chuck's hand, "if your ever in London give me a ring. I'll get you something stronger than that" Harry rushed out, running towards the door with haste arriving at designated apparition point in the nick of time.

Sitting at the bar, a bemused look on his face Chuck Bass made a decision. Perhaps it's time he look to further his empire. London is the New York of England, and chatting up a curious green eyed man seemed like a much better time than wandering aimlessly around Paris with a broken heart.

 _Stranger Danger! Who's the mystery man who's caught C's eye, poor thing. I heard he not from around these parts, probably doesn't know what he's just got himself into, and what'll B have to say about London randeavous, nothing good I hope. Buckle in Harry, your in for a bumpy ride._

 _XOXO Gossip Girl_


	2. Chapter 2

"Nate!" Jenny called out to the seemingly empty penthouse. She sighed, not expecting a reply and preparing to turn around and get a headstart to Hudson. Instead she was interrupted by a slightly slurring Chuck Bass who wore his ever present smirk, hiding some of the day's pain behind a shark like grin.

"He's not here." He said, leaning against his door frame a glass of amber liquid in his hand.

"Evidently," She replied, worriedly appraising his frenzied gaze and the light tremble of his hand. "Chuck, what are you doing?" She asked, gazing at the misplaced warmth the candle light coming from his room seemed to bathe the duo in.

"I'm trying to forget, trying to move on. I did the most romantic thing I could think of and it didn't work, it was never going to. There's nothing left for me here, I'm leaving." Chuck said, looking to the side, hurt so evident in his eyes. His earlier bravado all but disappeared. How fucked he thought. In the face of a total stranger he was able to mask all his sorrows but he'd laid his heart bare for little Jenny Humphrey. It was disgusting.

Jenny cleared her throat bringing him back from his thoughts. "Well, if Nate's not here, I guess I'll go. Not that I have anywhere to go." She mused, frowning, trying to clear her head of everything she'd seem to have lost. All the relationships she had managed to fuck up in such a short amount of time.

"You could come with, if you'd like" Chuck offered, misery always enjoys company "I'm going to London to expand my empire, and what's a boy billionaire without a private jet?"

Jenny thought about it, and couldn't really find it in herself to say no. It was such an easy out and all she wanted to do was run. "I'd love that," she said with a slight smile, moving towards Chuck "I could use some moving on too, I thought that this world was a fairytale," she snorted "but if it is I guess I'm just the wicked step sister."

"The world you're looking for only exists from the outside, the only reason I survive in it is because I always knew that it was empty" Chuck said handing her the glass and turning back to his packing.

Jenny stared deep into the amber liquid as if she were desperate for answers before she finally gulped it back. "Do you need any help?" She asked, trying to keep her mind from drifting.

"I was actually just finishing, my ride should be outside now" he said zipping up his suitcase and placing it softly on the floor. "We'll make a quick detour to your place in brooklyn so you can grab some stuff and then we'll leave this place"

She smiled at that ready to leave this place and all the shitty decisions she just keeps making. "That's perfect." She said following him towards the exit and his waiting car. Neither of them knew just how close they'd come to bumping into Blair Waldorff, only missing her by seconds, seconds she spent looking only at her phone desperately trying to get Chuck to answer. When she makes it to his suite her heart breaks, the ringing of Chuck Bass's abandoned phone sounding eery amongst the deafening silence of the rooms.

When the duo arrive at the loft Jenny's quick to make sure Dan wasn't there before rushing to gather enough things to start fresh. Most of what she finds makes her feel like a ghost like everything she's done to this point could matter less, and that couldn't be any truer, she'd spent so long grasping at anything she could and now here she was. The thought was more than daunting. After a second of consideration she grabs the emergency cash she's been saving since she'd entered this world, even then a flicker of doubt had always been present.

She leaves her phone and a note, _I'm Sorry,_ is all it says. One last look at the place she grew up and she's gone, glad to be able to finally say goodbye. Chuck opens the door for her when she comes down and then they're off.

"When we get to London, we're going to be staying at a property of my fathers. Where he carried out some of his less than favorable affairs, there's no way he'd mention it to Lily. I was being serious about furthering my empire so you can help me or do whatever you please really."

"Chuck?" Jenny whispers into the silence of the car.

"Hmm?"

"Thank you."

 **Spotted! Little J riding off into the night with our favorite Basstard! Oh my! This day just keeps getting better and better, or worse I'd suppose if you're Blair Waldorff. You should have been faster B, even I know not to leave a (B)ass hanging. And honestly what did you expect, maybe not this but the upper east side always did know how to throw a good curveball.**

 **You know you love me, xoxo Gossip Girl**

So here's part 2 I guess. This was supposed to be a one shot but I've been busy. I like Jenny so she's going with. No worries shes not going to fuck shit up and she's certainly not gonna be paired with Harry or Chuck, either way I'm excited to write out some interactions she has and the person she becomes after leaving the UES. Also she's 17 and I honestly did the bare minimum research but apparently if a kid over the age of 17 runs away there's no legal action that can be taken, idk. I have no clue where this is going but Harry should be in the next chapter. Also I'm writing another GG/HP fanfic except this one gonna have a bit of avengers thrown in for some extra fun so we'll see how that goes.


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